Pyridinium, 1-fluoro-, 1,1,1-trifluoromethanesulfonate (1:1) → 2-(3-BROMO-1H-1,2,4-TRIAZOL-1-YL)PYRIDINE

Temperature

-78 °C

3-Bromo-1H-1,2,4triazole (1.9 g, 12.8 mmol) was dissolved in anhydrous methanol (20 mL). NaOMe (51 mL of a 0.5 M solution in methanol, 25.6 mmol) was then added to the stirred solution and the resulting reaction mixture was cooled to −78° C. in an argon blanketed flask. 1-Fluoropyridinium triflate (4.9 g, 15 mmol) in anhydrous methanol (20 mL) was added dropwise to this stirred solution. The resulting yellow mixture was stirred at −78° C. for 1 h under argon atmosphere, then allowed to reach ambient temperature. The mixture was stirred for 16 h at ambient temperature, after which time it was concentrated in vacuo. The resulting residue was dissolved in EtOAc (100 mL), the EtOAc solution washed with H2O (100 mL), then brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane:EtOAc (90:10) to afford 2-(3-bromo-1H-1,2,4-triazol-1-yl)pyridine as a white solid.

1. customthe resulting reaction mixture
2. customto reach ambient temperature
3. stirringThe mixture was stirred for 16 h at ambient temperature
4. concentrationafter which time it was concentrated in vacuo
5. dissolutionThe resulting residue was dissolved in EtOAc (100 mL)
6. washthe EtOAc solution washed with H2O (100 mL)
7. dry with materialbrine (100 mL), dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was chromatographed on silica gel eluting with hexane:EtOAc (90:10)

ORD record

ord-7d34cdf1c1b64b16aa317b5809540df7

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105548B2